Andy Roddick is one of the few players to have defeated all of the Big Three — Roger Federer, Rafael Nadal, and Novak Djokovic — at different points in his career.

The American has had a total of 11 wins over the three legends, a list in which he is joined by other prominent names such as Stan Wawrinka, Juan Martin Del Potro, Dominic Thiem, and the extension of the Big Three, Andy Murray, who joins the trio to form the Big Four.

Roddick held the World No. 1 ranking in 2003 before Federer won the Australian Open title in 2004 and ended his reign. It was the same year that marked the inception of the dominance of the Federer-Nadal era which was joined by Djokovic soon.

With 32 career singles titles, including a Grand Slam (2003 US Open) and three Wimbledon finals, Roddick is part of the list of some of the most talented players in the Open Era. He was inducted into the International Tennis Hall of Fame in 2017, five years after his retirement.

While his set of achievements speaks for himself, Roddick holds a 5-4 record against Djokovic, 3-7 against Nadal, and 3-21 against Federer, including some iconic clashes. Here are some of Roddick’s biggest wins over Djokovic, Federer, and Nadal.

#3 2009 Australian Open Quarterfinal against Djokovic

While Djokovic holds a massive record of 98 career titles as opposed to Roddick’s 32, the American finished his career with a 5-4 head-to-head lead over the Serb. However, out of the five victories that Roddick has over Djokovic, one that tends to stand out is the 2009 Australian Open quarterfinal.

Andy Roddick defeated the defending champion and the now record-holder of the maximum number of Australian Open titles, Novak Djokovic, 6-7, 6-4, 6-2, 2-1, as the latter was forced to retire due to the intense heat in Melbourne.